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There must be a point when it becomes unnatural, and could potentially hurt you. What do you think?
For example, the term 'long red widgets sale' will help rank for the following terms:
long red widgets sale
long red widgets
red widgets sale
By combining primary keywords in your anchor text (have a few that just say 'red widgets') with more long tail terms you will get a good variation of keywords while still ranking well for your primary keywords without looking overly spammy.